Catalytic hydrosilylation of terminal alkynes promoted by organoactinides

Organometallics

Volumn 18, Issue 23, 1999, Pages 4724-4741

  Dash, Aswini K ^a   Wang, Ji Quan ^a   Eisen, Moris S ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

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Indexed keywords

EID: 0001099690     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990655c     Document Type: Article

References (105)

1. For general organolanthanide reviews, see: (a) Anwander, R.; Herrman, W. A. Top. Curr. Chem. 1996, 179, 1. (b) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247. (c) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1895, 95, 865 and references therein. (d) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283 and references therein.
2. For general organolanthanide reviews, see: (a) Anwander, R.; Herrman, W. A. Top. Curr. Chem. 1996, 179, 1. (b) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247. (c) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1895, 95, 865 and references therein. (d) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283 and references therein.
3. For general organolanthanide reviews, see: (a) Anwander, R.; Herrman, W. A. Top. Curr. Chem. 1996, 179, 1. (b) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247. (c) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1895, 95, 865 and references therein. (d) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283 and references therein.
4. For general organolanthanide reviews, see: (a) Anwander, R.; Herrman, W. A. Top. Curr. Chem. 1996, 179, 1. (b) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247. (c) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1895, 95, 865 and references therein. (d) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283 and references therein.
5. For general organoactinide reviews, see: (a) Edelmann, F. T.; Gun'ko, Y. K. Coord. Chem. Rev. 1997, 165, 163. (b) Ephritikhine, M. New J. Chem. 1992, 16, 451. (c) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds. Pergamon Press: Oxford, U.K., 1995; Chapter 2.
6. For general organoactinide reviews, see: (a) Edelmann, F. T.; Gun'ko, Y. K. Coord. Chem. Rev. 1997, 165, 163. (b) Ephritikhine, M. New J. Chem. 1992, 16, 451. (c) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds. Pergamon Press: Oxford, U.K., 1995; Chapter 2.
7. For general organoactinide reviews, see: (a) Edelmann, F. T.; Gun'ko, Y. K. Coord. Chem. Rev. 1997, 165, 163. (b) Ephritikhine, M. New J. Chem. 1992, 16, 451. (c) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds. Pergamon Press: Oxford, U.K., 1995; Chapter 2.
8. For examples of the catalytic activity of organolanthanides in a variety of alkene and alkyne hydrogenations, see: (a) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486. (b) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 6, 4705. (c) Haar, C. M.; Stern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765. (d) Molander, G. A.; Winterfeld, J. J. Organomet. Chem. 1996, 524, 275. (e) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241.
9. For examples of the catalytic activity of organolanthanides in a variety of alkene and alkyne hydrogenations, see: (a) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486. (b) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 6, 4705. (c) Haar, C. M.; Stern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765. (d) Molander, G. A.; Winterfeld, J. J. Organomet. Chem. 1996, 524, 275. (e) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241.
10. For examples of the catalytic activity of organolanthanides in a variety of alkene and alkyne hydrogenations, see: (a) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486. (b) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 6, 4705. (c) Haar, C. M.; Stern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765. (d) Molander, G. A.; Winterfeld, J. J. Organomet. Chem. 1996, 524, 275. (e) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241.
11. For examples of the catalytic activity of organolanthanides in a variety of alkene and alkyne hydrogenations, see: (a) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486. (b) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 6, 4705. (c) Haar, C. M.; Stern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765. (d) Molander, G. A.; Winterfeld, J. J. Organomet. Chem. 1996, 524, 275. (e) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241.
12. For examples of the catalytic activity of organolanthanides in a variety of alkene and alkyne hydrogenations, see: (a) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486. (b) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 6, 4705. (c) Haar, C. M.; Stern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765. (d) Molander, G. A.; Winterfeld, J. J. Organomet. Chem. 1996, 524, 275. (e) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241.
13. For examples of the catalytic activity of organolanthanides in dimerization, oligomerization, or polymerization, see: (a) Boff, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (b) Evans, W. J.; DeCoster, P. M.; Greaves, J. Macromolecules 1995, 28, 7929. (c) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (d) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (e) Fu, P.-F.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 10747. (f) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495 and references therein.
14. For examples of the catalytic activity of organolanthanides in dimerization, oligomerization, or polymerization, see: (a) Boff, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (b) Evans, W. J.; DeCoster, P. M.; Greaves, J. Macromolecules 1995, 28, 7929. (c) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (d) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (e) Fu, P.-F.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 10747. (f) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495 and references therein.
15. For examples of the catalytic activity of organolanthanides in dimerization, oligomerization, or polymerization, see: (a) Boff, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (b) Evans, W. J.; DeCoster, P. M.; Greaves, J. Macromolecules 1995, 28, 7929. (c) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (d) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (e) Fu, P.-F.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 10747. (f) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495 and references therein.
16. For examples of the catalytic activity of organolanthanides in dimerization, oligomerization, or polymerization, see: (a) Boff, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (b) Evans, W. J.; DeCoster, P. M.; Greaves, J. Macromolecules 1995, 28, 7929. (c) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (d) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (e) Fu, P.-F.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 10747. (f) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495 and references therein.
17. For examples of the catalytic activity of organolanthanides in dimerization, oligomerization, or polymerization, see: (a) Boff, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (b) Evans, W. J.; DeCoster, P. M.; Greaves, J. Macromolecules 1995, 28, 7929. (c) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (d) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (e) Fu, P.-F.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 10747. (f) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495 and references therein.
18. For examples of the catalytic activity of organolanthanides in dimerization, oligomerization, or polymerization, see: (a) Boff, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (b) Evans, W. J.; DeCoster, P. M.; Greaves, J. Macromolecules 1995, 28, 7929. (c) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (d) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (e) Fu, P.-F.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 10747. (f) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495 and references therein.
19. For examples of the catalytic activity of organolanthanides in hydroamination, see: (a) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 4871. (b) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295. (c) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770. (d) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707 and references therein.
20. For examples of the catalytic activity of organolanthanides in hydroamination, see: (a) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 4871. (b) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295. (c) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770. (d) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707 and references therein.
21. For examples of the catalytic activity of organolanthanides in hydroamination, see: (a) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 4871. (b) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295. (c) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770. (d) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707 and references therein.
22. For examples of the catalytic activity of organolanthanides in hydroamination, see: (a) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 4871. (b) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295. (c) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770. (d) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707 and references therein.
23. For examples of catalytic activity of organolanthanides in hydrosilylation see: (a) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 117, 7157. (b) Schumann, H.; Keitsch, M. R.; Winterfeld, J.; Muhle, S.; Molander, G. A. J. Organomet. Chem. 1998, 559, 181. (c) Molander, G. A.; Dowdy, E. D.; Noll, B. C. Organometallics 1998, 17, 3754. (d) Onozawa, S.; Sakakura, T.; Tanaka, M. Tetrahedron Lett. 1994, 35, 8177.
24. For examples of catalytic activity of organolanthanides in hydrosilylation see: (a) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 117, 7157. (b) Schumann, H.; Keitsch, M. R.; Winterfeld, J.; Muhle, S.; Molander, G. A. J. Organomet. Chem. 1998, 559, 181. (c) Molander, G. A.; Dowdy, E. D.; Noll, B. C. Organometallics 1998, 17, 3754. (d) Onozawa, S.; Sakakura, T.; Tanaka, M. Tetrahedron Lett. 1994, 35, 8177.
25. For examples of catalytic activity of organolanthanides in hydrosilylation see: (a) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 117, 7157. (b) Schumann, H.; Keitsch, M. R.; Winterfeld, J.; Muhle, S.; Molander, G. A. J. Organomet. Chem. 1998, 559, 181. (c) Molander, G. A.; Dowdy, E. D.; Noll, B. C. Organometallics 1998, 17, 3754. (d) Onozawa, S.; Sakakura, T.; Tanaka, M. Tetrahedron Lett. 1994, 35, 8177.
26. For examples of catalytic activity of organolanthanides in hydrosilylation see: (a) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 117, 7157. (b) Schumann, H.; Keitsch, M. R.; Winterfeld, J.; Muhle, S.; Molander, G. A. J. Organomet. Chem. 1998, 559, 181. (c) Molander, G. A.; Dowdy, E. D.; Noll, B. C. Organometallics 1998, 17, 3754. (d) Onozawa, S.; Sakakura, T.; Tanaka, M. Tetrahedron Lett. 1994, 35, 8177.
27. Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, The Netherlands, 1992; pp 35-54.
28. For examples of the catalytic activity of organolanthanides in hydroboration, see: (a) Anwander, R. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Hermann, W., Eds, VCH: Weinheim, Germany, 1997; Vol. 2, pp 866-892. (b) Bypost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. 1995, 95, 121. (c) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
29. For examples of the catalytic activity of organolanthanides in hydroboration, see: (a) Anwander, R. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Hermann, W., Eds, VCH: Weinheim, Germany, 1997; Vol. 2, pp 866-892. (b) Bypost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. 1995, 95, 121. (c) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
30. For examples of the catalytic activity of organolanthanides in hydroboration, see: (a) Anwander, R. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Hermann, W., Eds, VCH: Weinheim, Germany, 1997; Vol. 2, pp 866-892. (b) Bypost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. 1995, 95, 121. (c) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
31. Voskoboynikov, A. Z.; Beletskaya, I. P. New J. Chem. 1995, 19, 723.
32. For examples of the catalytic activity of organolanthanides in ring-opening Ziegler polymerizations, see: (a) Jia, L.; Yang, X.; Seyam, A. M.; Albert, I. D. L.; Fu, P.-F.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 7900. (b) Yang, X.; Seyam, A. M.; Fu, P.-F.; Marks, T. J. Macromolecules 1994, 27, 4625.
33. For examples of the catalytic activity of organolanthanides in ring-opening Ziegler polymerizations, see: (a) Jia, L.; Yang, X.; Seyam, A. M.; Albert, I. D. L.; Fu, P.-F.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 7900. (b) Yang, X.; Seyam, A. M.; Fu, P.-F.; Marks, T. J. Macromolecules 1994, 27, 4625.
34. For examples of the catalytic activity of organoactinidea in C-H activation processes, see: (a) Smith, G. M.; Carpenter, J. D.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 6805. (b) Fendrick, C. M.; Schertz, L. D.; Day, V. W.; Marks, T. J. J. Am. Chem. Soc. 1988, 7, 1828.
35. For examples of the catalytic activity of organoactinidea in C-H activation processes, see: (a) Smith, G. M.; Carpenter, J. D.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 6805. (b) Fendrick, C. M.; Schertz, L. D.; Day, V. W.; Marks, T. J. J. Am. Chem. Soc. 1988, 7, 1828.
36. Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515 and references therein.
37. For examples of the catalytic activity of organoactinides in hydroamination, see: (a) Haskel, A.; Straub, T.; Eisen, M. S. Organometallics 1996, 15, 3773. (b) Straub, T.; Frank, W.; Reiss, G. J.; Eisen. M. S. J. Chem. Soc., Dalton Trans. 1996, 2541.
38. For examples of the catalytic activity of organoactinides in hydroamination, see: (a) Haskel, A.; Straub, T.; Eisen, M. S. Organometallics 1996, 15, 3773. (b) Straub, T.; Frank, W.; Reiss, G. J.; Eisen. M. S. J. Chem. Soc., Dalton Trans. 1996, 2541.
39. For examples of the catalytic activity of organoactinides in oligomerizations, see: (a) Straub, T.; Haskel, A.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364. (b) Haskel, A.; Straub, T.; Dash, A. K.; Eisen, M. S. J. Am. Chem. Soc. 1999, 121, 3014. (c) Haskel, A.; Wang, J. Q.; Straub, T.; Gueta-Neyroud, T.; Eisen, M. S. J. Am. Chem. Soc. 1999, 121, 3025.
40. For examples of the catalytic activity of organoactinides in oligomerizations, see: (a) Straub, T.; Haskel, A.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364. (b) Haskel, A.; Straub, T.; Dash, A. K.; Eisen, M. S. J. Am. Chem. Soc. 1999, 121, 3014. (c) Haskel, A.; Wang, J. Q.; Straub, T.; Gueta-Neyroud, T.; Eisen, M. S. J. Am. Chem. Soc. 1999, 121, 3025.
41. For examples of the catalytic activity of organoactinides in oligomerizations, see: (a) Straub, T.; Haskel, A.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364. (b) Haskel, A.; Straub, T.; Dash, A. K.; Eisen, M. S. J. Am. Chem. Soc. 1999, 121, 3014. (c) Haskel, A.; Wang, J. Q.; Straub, T.; Gueta-Neyroud, T.; Eisen, M. S. J. Am. Chem. Soc. 1999, 121, 3025.
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57. For group 4 complexes, see: (a) Eisen, M. S. In The Chemistry of Organosilicon Compounds; Apeloig, Y., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1998; Vol. 2, Part 3, Chapter 35, pp 2038-2122. (b) Eisen, M. S. Rev. Inorg. Chem. 1997, 17, 25. (c) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. I. J. Am. Chem. Soc. 1991, 113, 8564. (d) Kesti, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095. (e) Corey, J. Y.; Zhu, X. H. Organometallics 1992, 11, 672 (f). Harrod, J. F.; Yun, S. S. Organometallics 1987, 6, 1381. For group 3 complexes, see: (g) Molander, G. A.; Retsch, W. H. Organometallics 1996, 14, 4570. (h) Molander, G. A.; Nichols, P. J.; Noll, B. C. J. Org. Chem. 1998, 63, 2292. (i) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
58. For group 4 complexes, see: (a) Eisen, M. S. In The Chemistry of Organosilicon Compounds; Apeloig, Y., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1998; Vol. 2, Part 3, Chapter 35, pp 2038-2122. (b) Eisen, M. S. Rev. Inorg. Chem. 1997, 17, 25. (c) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. I. J. Am. Chem. Soc. 1991, 113, 8564. (d) Kesti, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095. (e) Corey, J. Y.; Zhu, X. H. Organometallics 1992, 11, 672 (f). Harrod, J. F.; Yun, S. S. Organometallics 1987, 6, 1381. For group 3 complexes, see: (g) Molander, G. A.; Retsch, W. H. Organometallics 1996, 14, 4570. (h) Molander, G. A.; Nichols, P. J.; Noll, B. C. J. Org. Chem. 1998, 63, 2292. (i) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
59. For group 4 complexes, see: (a) Eisen, M. S. In The Chemistry of Organosilicon Compounds; Apeloig, Y., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1998; Vol. 2, Part 3, Chapter 35, pp 2038-2122. (b) Eisen, M. S. Rev. Inorg. Chem. 1997, 17, 25. (c) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. I. J. Am. Chem. Soc. 1991, 113, 8564. (d) Kesti, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095. (e) Corey, J. Y.; Zhu, X. H. Organometallics 1992, 11, 672 (f). Harrod, J. F.; Yun, S. S. Organometallics 1987, 6, 1381. For group 3 complexes, see: (g) Molander, G. A.; Retsch, W. H. Organometallics 1996, 14, 4570. (h) Molander, G. A.; Nichols, P. J.; Noll, B. C. J. Org. Chem. 1998, 63, 2292. (i) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
60. For group 4 complexes, see: (a) Eisen, M. S. In The Chemistry of Organosilicon Compounds; Apeloig, Y., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1998; Vol. 2, Part 3, Chapter 35, pp 2038-2122. (b) Eisen, M. S. Rev. Inorg. Chem. 1997, 17, 25. (c) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. I. J. Am. Chem. Soc. 1991, 113, 8564. (d) Kesti, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095. (e) Corey, J. Y.; Zhu, X. H. Organometallics 1992, 11, 672 (f). Harrod, J. F.; Yun, S. S. Organometallics 1987, 6, 1381. For group 3 complexes, see: (g) Molander, G. A.; Retsch, W. H. Organometallics 1996, 14, 4570. (h) Molander, G. A.; Nichols, P. J.; Noll, B. C. J. Org. Chem. 1998, 63, 2292. (i) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
61. For group 4 complexes, see: (a) Eisen, M. S. In The Chemistry of Organosilicon Compounds; Apeloig, Y., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1998; Vol. 2, Part 3, Chapter 35, pp 2038-2122. (b) Eisen, M. S. Rev. Inorg. Chem. 1997, 17, 25. (c) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. I. J. Am. Chem. Soc. 1991, 113, 8564. (d) Kesti, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095. (e) Corey, J. Y.; Zhu, X. H. Organometallics 1992, 11, 672 (f). Harrod, J. F.; Yun, S. S. Organometallics 1987, 6, 1381. For group 3 complexes, see: (g) Molander, G. A.; Retsch, W. H. Organometallics 1996, 14, 4570. (h) Molander, G. A.; Nichols, P. J.; Noll, B. C. J. Org. Chem. 1998, 63, 2292. (i) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
62. For group 4 complexes, see: (a) Eisen, M. S. In The Chemistry of Organosilicon Compounds; Apeloig, Y., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1998; Vol. 2, Part 3, Chapter 35, pp 2038-2122. (b) Eisen, M. S. Rev. Inorg. Chem. 1997, 17, 25. (c) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. I. J. Am. Chem. Soc. 1991, 113, 8564. (d) Kesti, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095. (e) Corey, J. Y.; Zhu, X. H. Organometallics 1992, 11, 672 (f). Harrod, J. F.; Yun, S. S. Organometallics 1987, 6, 1381. For group 3 complexes, see: (g) Molander, G. A.; Retsch, W. H. Organometallics 1996, 14, 4570. (h) Molander, G. A.; Nichols, P. J.; Noll, B. C. J. Org. Chem. 1998, 63, 2292. (i) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
63. For group 4 complexes, see: (a) Eisen, M. S. In The Chemistry of Organosilicon Compounds; Apeloig, Y., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1998; Vol. 2, Part 3, Chapter 35, pp 2038-2122. (b) Eisen, M. S. Rev. Inorg. Chem. 1997, 17, 25. (c) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. I. J. Am. Chem. Soc. 1991, 113, 8564. (d) Kesti, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095. (e) Corey, J. Y.; Zhu, X. H. Organometallics 1992, 11, 672 (f). Harrod, J. F.; Yun, S. S. Organometallics 1987, 6, 1381. For group 3 complexes, see: (g) Molander, G. A.; Retsch, W. H. Organometallics 1996, 14, 4570. (h) Molander, G. A.; Nichols, P. J.; Noll, B. C. J. Org. Chem. 1998, 63, 2292. (i) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
64. For group 4 complexes, see: (a) Eisen, M. S. In The Chemistry of Organosilicon Compounds; Apeloig, Y., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1998; Vol. 2, Part 3, Chapter 35, pp 2038-2122. (b) Eisen, M. S. Rev. Inorg. Chem. 1997, 17, 25. (c) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. I. J. Am. Chem. Soc. 1991, 113, 8564. (d) Kesti, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095. (e) Corey, J. Y.; Zhu, X. H. Organometallics 1992, 11, 672 (f). Harrod, J. F.; Yun, S. S. Organometallics 1987, 6, 1381. For group 3 complexes, see: (g) Molander, G. A.; Retsch, W. H. Organometallics 1996, 14, 4570. (h) Molander, G. A.; Nichols, P. J.; Noll, B. C. J. Org. Chem. 1998, 63, 2292. (i) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
65. For group 4 complexes, see: (a) Eisen, M. S. In The Chemistry of Organosilicon Compounds; Apeloig, Y., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1998; Vol. 2, Part 3, Chapter 35, pp 2038-2122. (b) Eisen, M. S. Rev. Inorg. Chem. 1997, 17, 25. (c) Takahashi, T.; Hasegawa, M.; Suzuki, N.; Saburi, M.; Rousset, C. J.; Fanwick, P. E.; Negishi, E. I. J. Am. Chem. Soc. 1991, 113, 8564. (d) Kesti, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095. (e) Corey, J. Y.; Zhu, X. H. Organometallics 1992, 11, 672 (f). Harrod, J. F.; Yun, S. S. Organometallics 1987, 6, 1381. For group 3 complexes, see: (g) Molander, G. A.; Retsch, W. H. Organometallics 1996, 14, 4570. (h) Molander, G. A.; Nichols, P. J.; Noll, B. C. J. Org. Chem. 1998, 63, 2292. (i) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
66. (a) Fleming, I.; Dunogues, J.; Smithers, R. H. Org. React. 1989, 37, 57.
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75. (a) Tanke, R. S.; Crabtree, R. H. Organometallics 1991, 10, 415.
76. (b) Takeuchi, R.; Yasue, H. Organometallics 1996, 15, 2098.
77. (c) Christ, M. L.; Sabo-Etienne, S.; Chaudert, B. Organometallics 1995, 74, 1082.
78. Three main modified Chalk-Harrod mechanisms have been postulated: (a) Seitz, F.; Wrighton, M. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 289. (b) Duckett, S. B.; Perutz, R. N. Organometallics 1992, 11, 90. (c) Ruiz, J.; Bentz, P. O.; Mann, B. E.; Spencer, C. M.; Taylor, B. F.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1987, 2709. (d) Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151.
79. Three main modified Chalk-Harrod mechanisms have been postulated: (a) Seitz, F.; Wrighton, M. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 289. (b) Duckett, S. B.; Perutz, R. N. Organometallics 1992, 11, 90. (c) Ruiz, J.; Bentz, P. O.; Mann, B. E.; Spencer, C. M.; Taylor, B. F.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1987, 2709. (d) Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151.
80. Three main modified Chalk-Harrod mechanisms have been postulated: (a) Seitz, F.; Wrighton, M. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 289. (b) Duckett, S. B.; Perutz, R. N. Organometallics 1992, 11, 90. (c) Ruiz, J.; Bentz, P. O.; Mann, B. E.; Spencer, C. M.; Taylor, B. F.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1987, 2709. (d) Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151.
81. Three main modified Chalk-Harrod mechanisms have been postulated: (a) Seitz, F.; Wrighton, M. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 289. (b) Duckett, S. B.; Perutz, R. N. Organometallics 1992, 11, 90. (c) Ruiz, J.; Bentz, P. O.; Mann, B. E.; Spencer, C. M.; Taylor, B. F.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1987, 2709. (d) Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151.
82. (a) Bode, B. M.; Day, P. N.; Gordon, M. S. J. Am. Chem. Soc. 1998, 120, 1552.
83. (b) Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510.
84. (c) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. J. Am. Chem. Soc. 1994, 116, 7258.
85. (a) Fagan, P. J.; Manriquez, J. M.; Maatta, E. A.; Seyam, A. M.; Marks, T. J. J. Am. Chem. Soc. 1981, 103, 6650.
86. (b) Aitken, C.; Barry, J. P.; Gauvin, F. G.; Harrod, J. F.; Malek, A.; Rousseau, D. Organometallics 1989, 8, 1732.
87. See the Supporting Information for kinetic and thermodynamic plots.
88. (a) King, W. A.; Marks, T. J. Inorg. Chim. Acta 1995, 229, 343.
89. (b) Radu, N. S.; Engeler, M. P.; Gerlach, C. P.; Tilley, T. D.; Rheingold, A. L. J. Am. Chem. Soc. 1995, 117, 3261.
90. (a) Nolan, S. P.; Stern, D.; Hedden, D.; Marks, T. J. ACS Symp. Ser. 1990, 428, 159.
91. (b) Marthino Simoes, J. A.; Beauchamp, J. L. Chem. Rev. 1990, 90, 629.
92. (c) Nolan, S. P.; Stern, D.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 7844.
93. For related group IV bis(acetylide) compounds, see: (a) Erker, G.; Frömberg, W.; Benn, R.; Mynott, R.; Augermund, K.; Krüger, C. Organometallics 1989, 8, 911. (b) Lang, H.; Herres, M.; Zsolnai, L.; Imhof, W. J. Organomet. Chem. 1991, 409, C7.
94. For related group IV bis(acetylide) compounds, see: (a) Erker, G.; Frömberg, W.; Benn, R.; Mynott, R.; Augermund, K.; Krüger, C. Organometallics 1989, 8, 911. (b) Lang, H.; Herres, M.; Zsolnai, L.; Imhof, W. J. Organomet. Chem. 1991, 409, C7.
95. Southard, G. E.; Curtis, M. D.; Kampf, J. W. Organometallics 1998, 15, 5, 4667.
96. For reviews, see: (a) Fleming, I. CHEMTRACTS: Org. Chem. 1993, 6, 113. (b) Apeloig, Y. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley-Interscienee: New York, 1989; pp 57-225. (c) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838 and references therein.
97. For reviews, see: (a) Fleming, I. CHEMTRACTS: Org. Chem. 1993, 6, 113. (b) Apeloig, Y. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley-Interscienee: New York, 1989; pp 57-225. (c) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838 and references therein.
98. For reviews, see: (a) Fleming, I. CHEMTRACTS: Org. Chem. 1993, 6, 113. (b) Apeloig, Y. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley-Interscienee: New York, 1989; pp 57-225. (c) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838 and references therein.
99. 6,19
100. The bis-silylation of a C-C triple bond is a reaction in which two Si-C bonds are created in the same molecule. Palladium complexes are the most often used catalysts. The mechanism consists of the oxidative addition of the Si-Si bond to palladium(0) and the transfer of the two organosilyl groups to the C-C triple bond in a cis stereochemistry, regenerating the palladium(0). See ref 19a and: (a) Murakami, M.; Yoshida, T.; Ito, Y. Orgunometallics 1994, 13, 2900. (b) Murakami, M.; Yoshida, T.; Kawanami, S.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 6408. (c) Ozawa, F.; Sugawara, M.; Hayashi, T. Organometallics 1994, 13, 3237. (d) Jacobsen, H.; Ziegler, T. Organometallics 1995, 14, 224.
101. The bis-silylation of a C-C triple bond is a reaction in which two Si-C bonds are created in the same molecule. Palladium complexes are the most often used catalysts. The mechanism consists of the oxidative addition of the Si-Si bond to palladium(0) and the transfer of the two organosilyl groups to the C-C triple bond in a cis stereochemistry, regenerating the palladium(0). See ref 19a and: (a) Murakami, M.; Yoshida, T.; Ito, Y. Orgunometallics 1994, 13, 2900. (b) Murakami, M.; Yoshida, T.; Kawanami, S.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 6408. (c) Ozawa, F.; Sugawara, M.; Hayashi, T. Organometallics 1994, 13, 3237. (d) Jacobsen, H.; Ziegler, T. Organometallics 1995, 14, 224.
102. The bis-silylation of a C-C triple bond is a reaction in which two Si-C bonds are created in the same molecule. Palladium complexes are the most often used catalysts. The mechanism consists of the oxidative addition of the Si-Si bond to palladium(0) and the transfer of the two organosilyl groups to the C-C triple bond in a cis stereochemistry, regenerating the palladium(0). See ref 19a and: (a) Murakami, M.; Yoshida, T.; Ito, Y. Orgunometallics 1994, 13, 2900. (b) Murakami, M.; Yoshida, T.; Kawanami, S.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 6408. (c) Ozawa, F.; Sugawara, M.; Hayashi, T. Organometallics 1994, 13, 3237. (d) Jacobsen, H.; Ziegler, T. Organometallics 1995, 14, 224.
103. The bis-silylation of a C-C triple bond is a reaction in which two Si-C bonds are created in the same molecule. Palladium complexes are the most often used catalysts. The mechanism consists of the oxidative addition of the Si-Si bond to palladium(0) and the transfer of the two organosilyl groups to the C-C triple bond in a cis stereochemistry, regenerating the palladium(0). See ref 19a and: (a) Murakami, M.; Yoshida, T.; Ito, Y. Orgunometallics 1994, 13, 2900. (b) Murakami, M.; Yoshida, T.; Kawanami, S.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 6408. (c) Ozawa, F.; Sugawara, M.; Hayashi, T. Organometallics 1994, 13, 3237. (d) Jacobsen, H.; Ziegler, T. Organometallics 1995, 14, 224.
104. 3, yielding the corresponding hydride.
105. Bassindale, A. R.; Glynn, S. J.; Taylor, P. G In The Chemistry of Organic Silicon Compounds; Apeloig, Y., Rappoport, Z., Eds.; Wiley: Chicheeter, U.K., 1998; Vol. 2, Part 1, Chapter 7, pp 355-430.